p-Toluenesulfonic acid → HCID 53932472, compound

HRID 2170258Notes

Reaction equation

HRID 2170258 reaction equation
[CH3:1][CH:2]([CH:10]=[CH:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH:3](OCC)[O:4]CC.O1CCCC1.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O>[CH3:1][CH:2]([CH:10]=[CH:11][CH:12]=[C:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH:3]=[O:4]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 78137770HCID 78137770, compound

Product 1

HCID 53932472HCID 53932472, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
22.5 °C

Procedure

To a 250 mL four-neck reaction flask protected from atmospheric moisture by nitrogen gas throughout the course of the reaction a solution of 14.0 g 2,6,10-trimethyl-1,1-diethoxy-3,5,9-undecatriene (2D, 0.05 mol), 100 mL tetrahydrofuran and 1.2 g of PTSA was added. After stirred until homogeneous, 22 g of water was added, and further 24 h of stirring at 20-25° C. was needed until the reaction completed according to GC. Then a solution of 2 g of NaHCO3 in 20 mL water was added for neutralization. Removal of THF by vacuum distillation, 100 mL of cyclohexane was added and then stratification. The organic layer was washed with 30 mL of water, dried over anhydrous magnesium sulfate and subsequently filtered. Removal of the volatile organic solvents by evaporation at reduced pressure afforded 10.3 g of crude 2,6,10-trimethyl-3,5,9-undecatriene-1-aldehyde of formula (12).

Workup

  1. additionwas added
  2. additionwas added
  3. customRemoval of THF
  4. distillationby vacuum distillation, 100 mL of cyclohexane
  5. additionwas added
  6. washThe organic layer was washed with 30 mL of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationsubsequently filtered
  9. customRemoval of the volatile organic solvents
  10. customby evaporation at reduced pressure

Sources & evidence

ORD record
ord-04d95e230a5140da86a19205606ebd94
Source dataset
uspto-grants-2015_06
Patent number
US09051254B2

Reaction notes

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